Abstract
A mild gold-catalyzed protodeboronation reaction, which does not require acid or base additives and can be carried out in "green" solvents, is described. As a result, the reaction is very functional-group-tolerant, even to acid- and base-sensitive functional groups, and should allow for the boronic acid group to be used as an effective traceless directing or blocking group. The reaction has also been extended to deuterodeboronations for regiospecific ipso-deuterations of aryls and heteroaryls from the corresponding organoboronic acid. Based on density functional theory calculations, a mechanism is proposed that involves nucleophilic attack of water at boron followed by rate-limiting B-C bond cleavage and facile protonolysis of a Au-σ-phenyl intermediate.
Original language | English |
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Pages (from-to) | 9807-9816 |
Number of pages | 10 |
Journal | Journal of Organic Chemistry |
Volume | 80 |
Issue number | 20 |
Early online date | 28 Jun 2015 |
DOIs | |
Publication status | Published - 16 Oct 2015 |
ASJC Scopus subject areas
- Organic Chemistry
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Supporting Information for: Gold-Catalyzed Proto- and Deutero-deboronation
Lee, A. (Creator), American Chemical Society, 15 Jul 2015
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Profiles
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Graeme Barker
- School of Engineering & Physical Sciences - Associate Professor
- School of Engineering & Physical Sciences, Institute of Chemical Sciences - Associate Professor
Person: Academic (Research & Teaching)